Diisopropylethylamine → 2-Naphthol

Participants

Reaction Steps

A solution of 12.6 g (0.031 mol) of [1R,2R]-(-)-2-[6-fluoro-1,2,3,4-tetrahydro-2-hydroxy-1-isopropyl-2-naphthyl]ethyl p-toluenesulphonate, 6.1 g (0.031 mol) of 3,4-(methylenedioxy)-N-methyl-β-phenethylamine and 5.3 ml (0.031 mol) of ethyldiisopropylamine in 50 ml of dimethyl sulfoxide was stirred under a nitrogen atmosphere for 3 hours at 80° and thereafter concentrated in a high vacuum. The residue was dissolved in methylene chloride and the solution obtained was washed with a saturated sodium carbonate solution and extracted three times with 3N hydrochloric acid. The aqueous extracts were made alkaline with a 28% sodium hydroxide solution. The oily suspension was extracted three times with methylene chloride. The organic extracts were dried and evaporated under reduced pressure. The residual oil was chromatographed on silica gel with ethyl acetate/methanol (9:1), yielding 9.3 g (73%) of [1R,2R]-(-)-6-fluoro-1,2,3,4-tetrahydro-1-isopropyl-2-[[3,4-(methylenedioxy)phenethyl]methylamino]ethyl]-2-naphthalenol as a yellowish oil; [α]D20 =-22.1°.

Provenance & Evidence